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Chester VT Real Estate

Located in Windsor County, Chester is a wonderful New England town reminiscent of a bygone era. With architecture pre-dating the civil war, Chester is rich in history and beauty. Although historic, the quaint town is thriving with its unique markets, galleries, and restaurants that offer much to do. The town is also conveniently located close to Okemo Mountain and Mount Snow for those who enjoy outdoor recreation as well as within driving distance to Manchester, VT

Search the latest real estate in Chester, VT with Maple Sweet Real Estate. Find the right property for you from a variety of listings. To save your favorites, register with us and you can get email notifications when similar properties are posted. Already have an account with us? Log in here.

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326 Goodrich Road Chester VT 05143

Chester, VT326 Goodrich Road

Price$8,600,000The price has recently decreased

MLS Number 4963698

  • Commercial
  • Year Built 2019
  • Square Feet 1,760
  • Acreage 25.99
  • PricePerSqFt 4886.36

This is a first class stone quarry operation which pumps out a beautiful stream of high grade gneiss stone, so indispensable for the building trades in constructing patios, steps, walls, chimneys, and every place beautifully ad naturally colored building stones are needed. The next owner of this business will of course be buying a highly profitable and proven going concern. However, the next owner will have seen the monumental opportunity in the $168,000,000, in unmined, and yet very minable stone as attested to by the attached professionally prepared geological report. Complete with $1.5 M worth of meticulously maintained equipment and an immaculate stone cutting shop, this offering spells opportunity writ large. While the Owner believes the next owner will be someone already in the industry, and he may be correct, I also believe that it could be anyone who sees the brilliance of buying assets for pennies on the currently shrinking and inflated dollar along with a proven and successful method for extracting same. But what do I know? I'm just a Realtor. But an entrepreurial MBA Realtor nonetheless who will be happy to show you this opportunity in person.

Listed by Lawrence Zupan of EXP Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

686 Green Mountain Turnpike Chester VT 05143

Chester, VT686 Green Mountain Turnpike

Price$999,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4995878

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 2,680

This charming home in Chester combines Vermont's rural charm with modern amenities. Surrounded by the serene beauty of Fox Chair Mountain, it offers an enchanting escape from daily life's hustle and bustle. Within the home, you'll find cozy spaces perfect for relaxation. From the inviting great room that opens onto a beautiful stone patio to the tranquil library, or the large private deck off the primary suite, and even the attached horse barn, there are several private areas to unwind and rejuvenate in this retreat. With two fireplaces and a wood stove, this home ensures comfort year-round. The modern kitchen is central to the flowing home and the porches and stone patio make gathering with friends and family a breeze whether it be an intimate dinner or a large crowd. The home's eastern exposure over a stunning alpine valley provides endless opportunities to appreciate Vermont's natural beauty. With a rich history as a working farm, this property is ready for its next chapter. This scenic 90+/- acres of stunning land, which is enrolled in the current use forestry program also has an outdoor riding arena, and perhaps an opportunity to create additional building lots in the future. Additionally the home can be purchased with just 3 acres. See MLS# 4995602. Whichever you choose you will find yourself poised for the enriching experience of living in this captivating haven. Don't miss the chance to create your sanctuary in Vermont. Schedule a viewing today!!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

233 Dodge Road Chester VT 05143

Chester, VT233 Dodge Road

Price$799,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4985500

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 4,532

Nestled on a picturesque 3.6-acre lot, this expansive Colonial home offers the epitome of Vermont living. Boasting 6 bedrooms, the residence exudes comfort and space. The heart of the home is the generous kitchen with an island, abundant counter space, and cabinets, all adorned with elegant granite countertops. Entertain in the large dining room or relax in the spacious living room that seamlessly flows to the front deck, bringing the outdoors in. An inviting sunroom opens to a very private back deck featuring a rejuvenating hot tub. The new walkout basement entrance leads to a convenient mudroom with ample ski storage, making winter adventures a breeze. The basement encompasses a recreational room with extra sleeping quarters and a delightful game room, offering endless entertainment options. An attached oversized garage provides convenience and additional storage. Beyond the main residence, a substantial barn accommodates equipment and toys, while an attached cottage offers the potential for restoration into a charming playhouse or office. This turnkey offering includes full furnishings, ensuring a seamless transition into your new abode. Secluded and serene, yet just a half mile from town, this property provides the perfect balance of tranquility and accessibility. Enjoy a short 15-minute drive to Okemo Mountain and easy access to other major resorts. Immerse yourself in the Vermont experience at its finest, embracing the beauty and charm this property has to offer.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

686 Green Mountain Turnpike Chester VT 05143

Chester, VT686 Green Mountain Turnpike

Price$789,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4995602

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 2,680

This charming home in Chester combines Vermont's rural charm with modern amenities. Surrounded by the serene beauty of Fox Chair Mountain, it offers an enchanting escape from daily life's hustle and bustle. Within the home, you'll find cozy spaces perfect for relaxation. From the inviting great room that opens onto a beautiful stone patio to the tranquil library, or the large private deck off the primary suite, and even the attached horse barn, there are several private areas to unwind and rejuvenate in this retreat. With two fireplaces and a wood stove, this home ensures comfort year-round. The modern kitchen is central to the flowing home and the porches and stone patio make gathering with friends and family a breeze whether it be an intimate dinner or a large crowd. The home's southern exposure over a stunning alpine valley provides endless opportunities to appreciate Vermont's natural beauty. With a rich history as a working farm, this property is ready for its next chapter. Additionally, beyond the 3-acre home site being offered is the opportunity to own a further 90+/- acres of stunning land with an outdoor riding arena, and perhaps an opportunity to create additional building lots. Whichever you choose you will find yourself poised for the enriching experience of living in this captivating haven. Don't miss the chance to create your sanctuary in Vermont. Schedule a viewing today and explore the possibilities of this pastoral paradise.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

559 Davidson Hill Road Chester VT 05143

Chester, VT559 Davidson Hill Road

Price$699,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4996384

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,356

Luxurious contemporary home in a naturalized setting. Beautiful mountain views from family room and expansive deck. This home is a unique blend of country charm and modern convenience. Everyone will gather round the large center island in this amazing kitchen designed for cooking and entertaining. Open concept floor plan flows from kitchen to dining area and into the family room where you can set and take in the mountain views beyond. Slider leads to the deck combining indoor and outdoor living space. A private den is connected to the family room with French doors and can be opened up for addition living space or closed off for a quiet retreat. Second floor has three generous sized bedrooms, two of which are en suites. There is also a bonus room on the second floor that can be used for crafts, or additional den, home office or playroom. Wired for generator as well. Currently used as a family getaway and AirBNB. Just 18 minutes to the ski lifts at Okemo. This property is sold "AS IS" with right to inspections.

Listed by Julie Buffum of Buffum Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

4877 Vt Route 103 Chester VT 05143

Chester, VT4877 Vt Route 103

Price$675,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4986618

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,728

Looking for the perfect ready to move in home in Vermont? This beautiful home is centrally located in the quiet town of Chester, Vermont on Route 103. Close to many ski mountains, within 10 minutes to Okemo mountain. House features a beautiful indoor and outdoor fireplace, outside hot tub, beautiful stone patio, large private deck, 2 car garage, 4 bedrooms (but lots of room for more people), 2 bathrooms, a bonus bunk room, 2 extra lofts for an office or library, extra recreation room, and paved driveway. The house is a short distance to several beautiful lakes, mountains to hike, near the VAST trails, and interstate 91. Very spacious and also currently a great short term rental income property. And if you happen to lose power there is a 20kw stand-by propane generator ready to go. Call for a showing today!

Listed by Erin Kendall of EXP Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

341 Whitmore Brook Road Chester VT 05143

Chester, VT341 Whitmore Brook Road

Price$645,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4981700

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,400

With it's stone fireplace, exposed beams, and textured logs, this home offers an authentic connection to the great outdoors. For nature enthusiasts, the property's proximity to Okemo Mountain, hiking trails, VAST trails, golf courses, and swimming spots is unbeatable, all within 8 miles. Tucked away on Whitmore Road just up off of 103, this home offers privacy in a serene setting, yet still very close to all amenities. Though the house itself requires some tender loving care, it presents an exciting opportunity for those with vision and ambition. Picture transforming the spacious living area with its impressive stone fireplace to match your unique style. Cathedral ceilings create an expansive and airy ambiance. A designated area with a bar offers the potential to create a remarkable entertainment space. Adjacent to the house, a poured foundation awaits your creative touch, approved for a barn or additional structure. Whether you choose to complete the vision or let your imagination run wild, this property offers endless possibilities for customization and personalization. Escape the hustle and bustle of modern life and envision your own Vermont retreat in this charming log home. Schedule a showing today and take the first step toward turning your vision into reality.

Listed by Frank Provance and Dana Haley of Diamond Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1573 Trebo Road Chester VT 05143

Chester, VT1573 Trebo Road

Price$599,950The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4995628

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,166

Picture yourself in a boat on a river... in this case a magnificent spring fed pond with a charming 2 bedroom, 2.5 bath log home on 6.5 +/- acres and a captivating view. The dramatic 19' deep pond features thoughtful stone scaping, an aerator and an amphitheater for picnics, swims, bonfires and nature watching. A family of ducks nest on the stone island each Spring and turtles, the smallest named Tea Leaf, bask on the rocks. The comfortable ranch style floor plan has a large kitchen which opens to the dining area with mini-split, an inviting living room with new wood flooring, a VT castings propane stove with granite hearth and a slider that opens to the covered deck overlooking the pond and view. A primary en suite bedroom overlooks the pond and a second bedroom is nearby a second full bath. The lower walkout level features custom sliding doors made from reclaimed barn boards, a finished living/tv area with woodstove and an English cottage inspired parlor with stained glass accent window and half bath that walks out to a hot tub tucked under the deck. A mudroom entry/breezeway leads to the two-car heated garage with excellent work space. The standby generator keeps the systems running providing peace of mind. A lovely custom built chicken coop will accommodate your brood of chickens and/or ducks who will love to splash in the pond! A wooded area provides additional privacy and walks in the woods. Close to skiing, shopping yet away from it all!

Listed by Geralyn Donohue of Engel & Volkers Okemo

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

46 Vt Route 103 S Chester VT 05143

Chester, VT46 Vt Route 103 S

Price$599,000The price has recently decreased

MLS Number 4965884

  • Commercial
  • Year Built 1966
  • Square Feet 1,316
  • Acreage 0.59
  • Area Commercial Zoning

The Country Girl Diner - a genuine Silk City Silver dining car (serial #178). The diner; recently featured in Yankee magazine "20 Diners Worth The Drive" issue, offers a rich history dating back to 1944 when it was built in Patterson, New Jersey. Located in the charming town of Chester, Vermont, this iconic diner has been a beloved part of the community since 1966. While a kitchen has been thoughtfully added to the rear of the diner to cater to modern needs, The Country Girl Diner still exudes a nostalgic ambiance that sets it apart from contemporary eateries. The unique blend of history and culinary delights makes it a truly one-of-a-kind destination. Don't miss the opportunity to own and cherish this piece of living history. The owners have updated and maintained this beautiful structure with love and care over the years and are ready to hand it over to someone new who has a passion for the restaurant industry. Whether you're a diner enthusiast, a lover of tradition, or seeking a business venture with character, The Country Girl Diner awaits you!

Listed by Craig Ruggless and Kate Barry of EXP Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

12 Common Street Chester VT 05143

Chester, VT12 Common Street

Price$485,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4990677

  • Multifamily
  • Units 3
  • Bathroom 1
  • Acreage 0.25
  • Square Feet 4,060

Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential! The first being the business store front, second is a space in the back which could easily be turned into a rental with a kitchen and separate bathroom, the third is a second floor 2bedroom 1 bathroom which has recently been updated with a freshly painted interior as well as new flooring and other updates. Along with the many benefits of this property's location comes parking right on the Green. Some recent updates are the back portion on the building has a new roof and solar was added to the whole building recently as well.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

3590 Vt 103 North Chester VT 05143

Chester, VT3590 Vt 103 North, Unit 505004

Price$479,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4994539

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,702

“Fully furnished! This home on .89 acres is located in the beautiful area of Gassetts in Chester, Vermont. Zoning is versatile and provides a wide range of options for commercial, retail, residential, or industrial use. Recent upgrades to the home include a brand new roof, siding, all new flooring, new kitchen cabinets and quarts countertops, new sheetrock and paint in the majority of the house, new sub flooring in the living room, laundry area, and mudroom, new window sills, new mini split, removal of all previous knob and tube wiring, replaced windows, new french door in the living room, new patio and fire pit area, freshly leveled and graveled driveway, two-car carport, refinished front deck, and freshly leveled backyard. This three bedroom, two bathroom home has an open concept as well as a traditional rustic ambiance with a beautiful modern touch. The three bedrooms are located on the second floor, with one bathroom being on the first floor as well as the second. The home is a mere 5 minute drive to the down center or about 8 miles to Okemo Ski Resort in the other direction. Hiking, mountain biking, and snowmobiling trails surround the town, making this home ideal for anyone who enjoys the natural beauty of Vermont. High speed internet is available (currently VTEL). LET'S MAKE A DEAL on LOT MLS# 4994538

Listed by Kimberly Matson and Jessica Samples of BHG Masiello Keene

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

138 Farrar Road Chester VT 05143

Chester, VT138 Farrar Road

Price$395,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4994890

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,944

This lovely contemporary home set in a peaceful country setting on over 3 acres in the heart of ski country is calling out to you. This location beckons to you to enjoy all four seasons. Recently updated 3 bdrm - 2 bath home has been completely renovated top to bottom and inside and out. Right down to a brand-new septic system! The main level has open concept living that flows right out on to the wrap around deck to bring the outside in now that Spring has finally arrived. You will enjoy the floor to ceiling stone fireplace to take the night chill off and a beautifully remodeled kitchen with all new appliances for those gatherings you will have to have. There is also a full bath on this level. Continue on up to the second level where you will find two very good-sized bedrooms and a 3/4 bath. Then you can go on down to the bottom level - where you will find the third bedroom, a den/office and the laundry is on this level as well. I could go on, but you have to call today and see for yourself what a lovely home and location it truly is.

Listed by Linda Benoit of Highland Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.02% last updated on 2024-05-16

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity 

Copyright 2024 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated May 22, 2024 7:09 AM EDT

 

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